The program is concerned with development of reactions and procedures in the carbohydrate field useful for synthesis of structures present in biologically important carbohydrate derivatives, and in understanding their biological role. A general objective is the establishment of reactions of high specificity that can be used, under mild conditions, for the structural conversion of common sugars and their derivatives into analogs of unusual functionality or stereochemistry that are present in numerous classes of natural carbohydrate derivatives, having importance in essential biological function and metabolism, or in therapeutic control. The reactions and procedures will facilitate partial and total syntheses of unusual sugars such as are present in various antibiotics, antitumor agents, components of bacterial cell walls, bacterial polysaccharides, physiologically active glycosides, and sugar derivatives involved in metabolism. Particular reactions for study include: specific oxidative procedures for introducing carbonyl functionality at selected sites in carbohydrates, synthetic procedures employing unsaturated functionality, reactions involving amination of sugars and transformations thereof, and transformations involving the dithioacetal group in sugar systems. Applications will include the total synthesis of various natural sugars, and the specific structural modification of physiologically active complex carbohydrates, such as antibiotics, as a lead to novel structures of modified biological response.